Contents
Introduction ............................................3 Product Profiles.......................................4 Ethylenediamine (EDA).........................4 Diethylenetriamine (DETA) ..................4 Triethylenetetramine (TETA) ................4 Tetraethylenepentamine (TEPA) ..........4 Heavy Polyamine (HPA) ........................5 Piperazine (PIP)......................................5 Aminoethylpiperazine (AEP) ................5 Aminoethylethanolamine (AEEA) ........5 Typical Physical Properties ....................6 Ethyleneamines Vapor Pressure vs. Temperature ........8 Viscosity vs. Temperature...................9 Specific Gravity vs. Temperature .....10 Ethylenediamine Aqueous Solutions Freezing Point vs. Composition.......11 Vapor-Liquid Equilibria at 760 mm Hg ................................12 Heat of Solution at 22°C ...................13 Specific Gravity vs. Temperature .....14 Piperazine Aqueous Solutions Freezing Point vs. Composition.......15 Vapor-Liquid Equilibria at 760 mm Hg ................................16 Reactions of Ethyleneamines...............17 Reaction Notes ......................................18 Ethyleneamines Applications ..............20 Major End-Uses....................................21 Lubricant and Fuel Additives..............22 Polyamide Resins .................................23 Asphalt Additives and Emulsifiers.......24 Petroleum Production and Refining....24 Resins and Additives for Pulp and Paper .....................................25 Epoxy Curing Agents............................26 Bleach Activators..................................26 Chelates and Chelating Agents...........27 Metal Ore Processing ...........................27 Surfactants and Emulsifiers ................28 Anthelmintics (Dewormers) ...............28 Fabric Softeners....................................29 Fungicides.............................................30 Textiles...................................................31 Polymers and Elastomers....................31 Other Applications ...............................31 Shipping Data........................................32 Product Specifications..........................32 Product Availability...............................33 Storage and Handling ...........................34 Health Effects ........................................35 Ecological Fate and Effects...................36 Product Safety .......................................37 FDA Status .............................................38 References .............................................40 Emergency Service................................47

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Introduction
he Dow Chemical Company, pioneered ethyleneamines development in 1935, when the company was the first to commercialize production, and has been the acknowledged world leader in the business ever since. Today, Dow manufactures ethyleneamines in two world-scale facilities at its Taft, Louisiana, petrochemicals complex. We are the only producer to use both the ethylene dichloride and reductive amination catalytic processes, thus providing unparalleled flexibility in meeting customer needs. Unexcelled quality – in product, technology, and services – is the byword of Dow’s ethyleneamines business. Another first for the company was receipt of ISO 9002 registration in 1990 for the Taft quality systems. Since then, registrations have been received for raw material quality systems, including those for ethylene, ethylene oxide, and ethanolamines, as well as for domestic and international distribution systems. In 1994, our ethyleneamines business won the Shingo Prize for Excellence in Manufacturing. The award recognizes outstanding achievements in manufacturing processes, quality enhancement, productivity improvement, and customer satisfaction. Helping to drive these evergreen quality programs is Dow’s technology leadership. Dedicated research and development focused on the ethyleneamines production processes has constantly improved product quality. Manufacturing technicians employ advanced statistical process control and zone charting for continuous improvement and reduced variability. Backing them is the in-plant laboratory with dedicated equipment for each of the ethyleneamines covered in this publication. And our applications scientists, unsurpassed in their knowledge of ethyl-eneamine end uses, are always ready to assist customers with their needs. Dow’s worldwide distribution network assures you of a readily available source of ethyleneamines.

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Product Profiles
Ethylenediamine (EDA) (1,2-diaminoethane) is the lowest molecular weight
member of the ethyleneamines family. It contains two primary amine groups and forms a maximum boiling azeotrope with water. H2NCH2CH2NH2 EDA is used primarily as an intermediate in the production of bleach activators, fungicides, chelating agents, plastic lubricants, textile resins, polyamides, and fuel additives.

Diethylenetriamine (DETA) is the second linear member of the ethyleneamines
family. It contains two primary and one secondary amine groups. Compared to ethylenediamine, DETA exhibits a broad liquid range: 207°C (405°F) boiling point at 760 mm Hg and -39°C (-38°F) freezing point. H2NCH2CH2NHCH2CH2NH2 DETA is used primarily as an intermediate to manufacture wet-strength paper resins, chelating agents, ion exchange resins, ore processing aids, textile softeners, fuel additives, and corrosion inhibitors.

Triethylenetetramine (TETA) is a liquid containing linear, branched, and cyclic
molecules. The principal tetramine structures are: H2NC2H4NHC2H4NHC2H4NH2 (H2NC2H4)3N HN NC2H4NHC2H4NH2 H2NC2H4N NC2H4NH2 Linear TETA Tris-aminoethylamine (TAEA) Piperazinoethylethylenediamine (PEEDA) Diaminoethylpiperazine (DAEP) (Bis-aminoethylpiperazine)

The major applications of TETA include epoxy curing agents, and the production of polyamides and oil and fuel additives.

Tetraethylenepentamine (TEPA) is a mixture containing linear, branched, and cyclic molecules. The structures of the major TEPA components are:
H2NC2H4NHC2H4NHC2H4NHC2H4NH2 H2NC2H4NHC2H4N(C2H4NH2)2 H2NC2H4NHC2H4N NC2H4NH2 HN NC2H4NHC2H4NHC2H4NH2 Linear TEPA Aminoethyltris-aminoethylamine (AE-TAEA) Aminoethyldiaminoethylpiperazine (AE-DAEP) Aminoethylpiperazinoethylethylenediamine (AE-PEEDA)

Among the major end-uses for TEPA are the preparation of oil and fuel additives, reactive polyamides, epoxy curing agents, and corrosion inhibitors.

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fabric softeners. and as an intermediate for the production of triethylenediamine polyurethane catalyst. chelates. together with the hydroxyl group. The major end-use applications for HPA include oil and fuel additives. The product has two secondary amine groups. the structures of which can be deduced from the chemistry of manufacture and a knowledge of the structures present in TETA and TEPA. polyamides. and coatings. corrosion inhibitors. an anhydrous piperazine is available in flake form. Since this narrow liquid range makes it difficult to handle. The primary and secondary amine groups. and one tertiary nitrogen atom. HN NC2H4NH2 Major end-uses for AEP include the production of urethane catalysts. Aminoethylethanolamine (AEEA) is an organic base with unique properties that make it an invaluable intermediate. In addition. and asphalt additives. The structures of the principal components contain six or more nitrogen atoms per molecule. HN NH Among the major applications for PIP are anthelmintics. branched. commercial piperazine is often sold in aqueous solutions to facilitate handling and storage. combine the features of an ethyleneamine and an ethanolamine. epoxy curing agents. Piperazine (PIP) is the simplest cyclic member of the ethyleneamines family.4 °F). Anhydrous PIP has a fairly high freezing point of 110°C (230°F) and a boiling point of 146°C (295°F) at 760 mm Hg. and asphalt additives.Heavy Polyamine (HPA) is a complex mixture of linear. AEP has a broad liquid range: boiling point of 222°C (432°F) at 760 mm Hg and a freezing point of -17°C (1. one secondary. and cyclic ethyleneamines. H2NC2H4NHC2H4OH Principal end-uses include surfactants. fuel additives. Aminoethylpiperazine (AEP) is unique among the ethyleneamines: it contains one primary. Note: “mlm” or “mlm” = –CH 2 CH 2 – 5 . pharmaceutical preparations.

% by wt 100 100 100(12) 100(12) 100(12) 100(10) 14 100 100 7.14(3) 86. 65% Piperazine.40 0.Typical Physical Properties Apparent Specific Gravity at 20/20°C 0.43 x 10-4 (3) 0. Anhydrous At 42°C/42°C At 130°C/20°C Pour point Ionization Constant.39 . Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) (2) (3) (4) (5) (6) Linear component only Typical molecular weight For Piperazine.10(7) < 0.21 104. at 25°C in Water 0.898 0.030 Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.015 1.24 9.45(6) Vapor Pressure at 20°C.35 .01 < 0.95 x 10-4 (2) 0.01 < 0.994 1.24(1) 189.63 x 10-4 10-4 (2) Dielectric Constant at 23°C 13.65 x 0.24 0.980 0.08 < 0.4(10) — (9) 0.32 8.32(6) 41 110 .952 0.01 Electrical Conductivity at 25°C.091 0.14 129.15 Freezing Point. ˚C 11 .036(4) 0.10 103.46(6) .877(5) 0.17 . K1.986 1.22 10.31 x (7) (8) (9) (10) (11) (12) 0.73 x 10-4 0.72 — — (9) (9) Solubility in Water at 20°C.007 0.01 < 0.40 x 0.30(1) 275(2) 86.13 19.63 10-4 10-4 7. micromhos/cm Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.17 146. with decomposition Solid at this condition At 42°C At 130°C Forms hydrate with time 6 .092 49. mm Hg 10.43 x 10-4 0.86 0.28 0. Anhydrous Aminoethylpiperazine Aminoethylethanolamine Molecular Weight 60.01 6.13 Vapor pressure of the solid Extrapolated.29 12. 65% Piperazine.52 0.72 x 10-4 (2) 0.

78(13) 0.9 127.501 1.14744 .6 134. heat of fusion 72. BTU/lb(16) .162(1) .74 cal/g At 130°C.68 0.045 — 0.139(1) — — .505 1.1 460. °C per mm Hg 0.Boiling Point. melting point 109.0 206.4 140.80 7.6°C.3 161.3 183 215 279(8) 54 — (9) 10 mm Hg 19.8 50 mm Hg 47.63 0.0 83.058 0. melting point 36°C.043 0.486 (13) (14) (15) (16) At 42°C.61 0. cP 1.16 26.52 0.499 1.049 Absolute Viscosity at 20°C.9 144 184 236 27 — (9) ∆ Boiling Point/∆p.4 88.14487 .14643 .403 . BTU/lb(15) 270 197 162 162 99 528 250 152 237 Heat of Combustion at 25°C.58 0.1 221.13910 . nD20°C 1.0 242.3 100.483 1.7 22.14353 .0 Refractive Index.64 Heat of Vaporization at 760 mm Hg.83 cal/g Estimated from vapor pressure using Clausius-Clapeyron equation Calculated from gross heat of combustion 7 .052 0.513 — — (9) (9) Specific Heat at 20°C.12395 Heat of Formation at 25°C.457 1.8 123.9261 . °C 760 mm Hg 117.1193 1.13251 .65 0. BTU/lb .9 277(8) 288(8) — 116 146. heat of fusion 50. 750-770 mm.056 0.036 0.304 .569 .256 .63(14) 0.14696 . cal/g•°C 0.73(11) 15.5(10) 0.037 0.

˚C 8 . ˚F 0 1000 800 600 500 400 300 PIP 200 20 40 80 120 160 200 240 320 400 480 560 Vapor Pressure. Vapor Pressure vs. mm Hg 100 80 60 50 40 30 20 10 8 6 5 4 3 2 EDA 65% PIP DETA AEP AEEA TETA TEPA UHP HPA X 1 -20 0 20 40 80 120 160 240 320 Temperature. Temperature Temperature.Figure 1: Ethyleneamines.

Figure 2: Ethyleneamines.0 EDA 1.0 Viscosity. ˚C 150 200 250 9 .0 65% PIP PIP 0.0 AEEA TEPA UHP 100.1 -50 0 50 100 Temperature. Viscosity vs.0 HPA X 1000. cP TETA AEP DETA 10. Temperature 10000.

00 AEP TETA DETA Specific Gravity. ˚C 10 .85 0.90 TEPA UHP PIP 0.80 0.05 AEEA 65% PIP HPA X 1.95 EDA 0. t˚C/20˚C 0. Specific Gravity vs.75 -20 20 60 100 140 180 220 260 Temperature.Figure 3: Ethyleneamines. Temperature 1.10 1.

Figure 4: Ethylenediamine Aqueous Solutions.8˚C -5 Temperature. Freezing Point vs. ˚C -15 -25 -35 -45 Eutectic -53.0˚C -55 0 10 20 30 40 50 60 70 80 90 100 Composition. Weight % Ethylenediamine 11 Composition of Monohydrate Composition of Dihydrate . Composition 15 5 Eutectic -0.

Vapor-Liquid Equilibria at 760 mm Hg 120 Vapor Phase 116 Liquid Phase Temperature.Figure 5: Ethylenediamine Aqueous Solutions. Mole % Ethylenediamine 12 . ˚C 112 108 104 100 0 10 20 30 40 50 60 70 80 90 100 Composition.

Weight % Water 13 . cal/gm of Solution 30 25 20 15 10 5 0 0 10 20 30 40 50 60 70 80 90 100 Composition. Heat of Solution at 22˚C 50 45 40 35 -∆ Hm.Figure 6: Ethylenediamine Aqueous Solutions.

Specific Gravity vs.90 0. Weight % Ethylenediamine 14 .00 0.94 0. Temperature 1.98 0.88 0 10 20 30 40 50 60 70 80 90 100 Composition.Figure 7: Ethylenediamine Aqueous Solutions.96 Specific Gravity at 20/20˚C 0.92 0.

Freezing Point vs.Figure 8: Piperazine Aqueous Solutions.% piperazine Composition of Hexahydrate 15 . Weight % Piperazine Studies show evidence of a metastable freezing point in the region of 20 wt. ˚C 60 40 Eutectic 33.2˚C 20 0 Eutectic -1˚C -20 0 10 20 30 40 50 60 70 80 90 100 Composition. Composition 120 100 80 Temperature.

˚C 125 Liquid Phase 120 115 110 105 100 95 0 10 20 30 40 50 60 70 80 90 100 Composition. Vapor-Liquid Equilibria at 760 mm Hg 150 145 140 135 Vapor Phase 130 Temperature.Figure 9: Piperazine Aqueous Solutions. Mole % Piperazine 16 .

Reactions of Ethyleneamines† † Illustrated by reactions of ethylenediamine (EDA). 17 . Other ethyleneamines react similarly. depending upon structure.

Monoamides can be cyclized to form imidazolines. . or acyl halides to form amidoamines and polyamides. Ethylenedinitramine. RX 5. .or liquid-phase reactions of ethyleneamines with glycols in the presence of several different metal oxide catalysts lead to predominantly cyclic ethyleneamine products (18). RX 4. to form mixtures of hydroxyalkyl derivatives (12-14). . RX 7. 18 .Alcohols and Alkylene Glycols Simple aliphatic alcohols can be used to alkylate ethyleneamines with hydrogen in the presence of a reductive amination catalyst (17). RX 2. RX 6. esters.Reaction Notes RX 1.3). is made by reacting one mole of EDA with two moles of nitric acid and splitting two moles of water from the salt at elevated temperatures (1) . . Product distribution is controlled by the amine-to-epoxide mole ratio. . an explosive compound. RX 3. This can be done without isolating the monoamide (4-8). acid anhydrides.Aziridines Aziridines react with ethyleneamines in an analogous fashion to epoxides (15-16). .Epoxides Ethyleneamines react readily with epoxides. .Nitriles Hydrogen cyanide (HCN) and aliphatic nitriles (RCN) can be used to form imidazolines (9-10). forming crystalline. Various diamides of EDA are prepared from the appropriate methyl ester or acid at moderate temperatures (2. Product distribution is controlled by the ethyleneamine-to-aziridine mole ratio. Either gas. water soluble salts.Organic Acids Ethyleneamines react with acids.Ureas Ethyleneamines react with urea to form substituted ureas and ammonia (11).Inorganic Acids Ethyleneamines react vigorously with commonly available inorganic acids.

RX 10. in concentrated aqueous solutions. NOx. Ethylene thiourea. . Ethyleneamines are soluble in water. reaction conditions. Reactions of aldehydes with such ethyleneamines as EDA or DETA give mono. . H2O. The hydrates of linear TETA and PIP melt around 50°C (25-26).Aldehydes Ethyleneamines react exothermically with aliphatic aldehydes. to form nitrosamine derivatives (24). 19 . and oxygen. RX 9. react with ethyleneamines to form various polymeric. However. or nitrous acid. activated by electron withdrawing groups. the reaction being mildly exothermic.Sulfur Compounds EDA reacts readily with two moles of carbon disulfide (CS2) in aqueous sodium hydroxide to form bis sodium dithiocarbamate.Environmental Reagents: CO2. depending on the reactant ratio (20). Carbon dioxide reacts readily with EDA in methanol to form crystalline N-(2-aminoethyl)carbamate (23). water-soluble cationic products or higher ethyleneamine products. crosslinked. metal complexation or choice of solvent. Mixing methylene chloride and EDA reportedly causes a runaway reaction (19). react with ethyleneamines to form mono.and disubstituted imidazolidines via cyclization of the intermediate Schiff base (21). nitrogen oxides. they are sufficiently reactive that upon exposure to adventitious water.RX 8. O2 Under normal conditions ethyleneamines are considered to be thermally stable molecules.or disubstituted derivatives. carbon dioxide. and structure of the ethyleneamine. Product distribution is controlled by reactant ratio. nitrites. N-Alkyl-piperazines and piperazine can react with nitrosating agents. The products depend on stoichiometry. such as ethylene dichloride. a suspect human carcinogen. However. . such as nitrogen oxides. . amine hydrates may form. Aliphatic dihalides.Halides Alkyl halides and aryl halides. trace levels of byproducts can form and increased color usually results. RX 11. which can be reacted with zinc (or manganese) to give the appropriate dithiocarbamate salt. is prepared by reacting CS2 in aqueous EDA (22).

They are predominantly used as intermediates in the production of functional products.Ethyleneamines Applications Ethyleneamines are utilized in a wide variety of applications because of their unique combination of reactivity. and surface activity. The following table lists the major end-use applications for these versatile materials. . basicity.

Major End-Uses for Ethyleneamines Application Lube Oil Additives Fuel Additives Polyamide Resins Asphalt Chemicals Corrosion Inhibitors Wet-Strength Paper Resins Epoxy Curing Agents Bleach Activators Chelating Agents Ore Flotation Agents Surfactants Fabric Softeners Fungicides Anthelmintics Spandex Fibers Urethanes Military Decontamination Agents Plastic Lubricants Ion Exchange Resins Coatings NOTE: The largest volume applications are indicated by ++ EDA DETA TETA TEPA Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine HPA PIP AEP AEEA Heavy Polyamine Piperazine Aminoethylpiperazine Aminoethylethanolamine EDA DETA + TETA + + ++ + + ++ TEPA ++ + ++ + + + ++ HPA ++ PIP AEP AEEA ++ ++ + + ++ ++ ++ + + ++ ++ + + ++ + + ++ ++ ++ + + ++ ++ ++ + + ++ + + + ++ ++ + + + ++ 21 .

by solubilizing oil-insoluble liquids. The higher molecular weight ethyleneamines are most popular for these derivatives.and bis-polyisobutenyl-succinimides.Lubricant and Fuel Additives The largest application area for ethyleneamines is in ashless dispersants for engine oils and other lubricants. 2) with ethyleneamines (3-44). all the ethyleneamines have been employed for various products (45). Besides the more common means of linking long-chain hydrophobic moieties to ethyleneamines via the succinimide linkage. The ethyleneamine derivatives most commonly employed for these tasks are the mono. Post-treatments of the succinimides are commonly utilized for performance improvement in engine oils (4658). The lubricant additives function mainly to reduce the formation of however. They are prepared on a commercial scale by reaction of an alkylphenol with formaldehyde and an ethyleneamine (71-76). a different linkage is employed in another important class of ashless dispersants – the Mannich bases (60-70). 22 . The alkyl and ethyleneamine moieties are similar to those used in the succinimide products. and in certain dispersantdetergents for fuels. varnish inhibitors for lubricating oils for twostroke engines (59). Ethyleneamines are also used in dispersant- sludge and varnish deposits within internal combustion engines by inhibiting the aggregation of particles. normally prepared by the condensation reaction of polyisobutenyl-succinic anhydrides (PIBSAs) (1. and by neutralizing acidic species formed in the combustion process.

pressure-sensitive. polyester. 80). Thermoplastic polyamides are similarly used in formulating glossy. 78). They are also used in preparing fatty acid/amine soaps and poly(urea) thickeners for lubricating greases. Being soluble in alcohol-based solvents and exhibiting outstanding adhesion to polyolefins. for example.Lubricant and Fuel Additives (cont’d) Additives for lubricating oils providing a combination of viscosity index improvement (VII) and dispersancy have also been reported. to provide a reaction site. and AEEA have found significant commercial application as dispersant detergent additives for gasoline when made by this route. overprint varnishes. Polyamide resins find wide use as binders in printing inks for flexogravure application on certain paper. in addition to the liquid resins used as epoxy hardeners. DETA. cellophane. however. Numerous similar products made generally by alkylating or acylating EDA or DETA (87-95) are also used as fuel detergent and deposit control additives. and metal. These polyamides are used in hot-melt. they are particularly suited to these applications. Cetane improvement in diesel fuels has been reported for a mixture containing EDA (96). 4). These additives are prepared from ethyleneamines by reaction with various viscosity index improvement polymers that have been modified. and foil webs (8). EDA is a principal amine reactant (1). and. abrasionresistant.and polybasic fatty acids. is that prepared generally by the condensation reaction of diamines with di. and heat-seal adhesives for leather. Dispersant-detergent additives useful in gasoline are prepared by the direct alkylation of ethyleneamines with chlorinated polybutenes (81-86). plastic. film. a number of antiwear/antiscuff additives for lube oils and greases also use ethyleneamines. Polyamide Resins The main polyamide resin type. 23 . paper. Anti-rust additives for lubricating oils have also been prepared by reacting ethyleneamines with fatty acids followed by reaction with polyalkylenesuccinic anhydrides (77. PIP and certain PIP derivatives are used with EDA in certain cases (3. EDA. tri. and as corrosion inhibitors in alkyd paints (7). to plasticize nitrocellulose lacquers (6). They are also used to modify alkyd resins in certain thixotropic coating systems (5). and paper. via chlorination.and tetramines are sometimes used at low levels to achieve specific performance (2). Oil additives providing detergent properties have also been prepared from ethyleneamines (79.

and bis-amidoamines. Similar ethyleneamine derivatives are used to make stable asphalt-in-water emulsions (8-16). They generally utilize the condensation reaction products of higher ethyleneamines and fatty or dimer acids. imidazolines. Petroleum Production and Refining A number of ethyleneamine derivatives are also employed in petroleum production and refining operations as corrosion inhibitors. Ethyleneamines are also employed in petroleum refining operations. In some secondary recovery operations. DETA. 13). and in the processing of certain catalysts (22-25). These films displace the corrosive production fluids and attract a film of petroleum which further isolates the steel from the fluid.Asphalt Additives and Emulsifiers Mono. 17). The oil-water emulsions generated at times by petroleum wells can often be broken with certain ethyleneamine derivatives (8-10) (EDA..e. mono. and pH and increase resistance to hydrolysis (15). and surfacing. These are generally used as their HCl or acetic acid salts. and polyamides. imidazolines. Corrosion inhibitor formulations for downhole petroleum production applications use a significant volume of ethyleneamines. to separate carbon disulfide from a pyrolysis fraction (21). and TETA. neutralizers. i. They are typically prepared from the higher molecular weight ethyleneamines and fatty acids (1-7). as part of a system used to extract thiols from petroleum distillates (18). They are usually applied to the petroleum well by any of several methods designed to create a film of inhibitor on the surfaces of the steel structures in the petroleum well. Typically. patching. ethyleneamines can be used to decrease the migration of injected chemicals into the formation by adsorption and precipitation (14). Antistrip additives promote adhesion between the mineral aggregate and the asphalt in mixtures for road paving. they are represented by the products made from DETA and fatty acids (1-7). TEPA and other ethyleneamines combined with thickeners help stabilize viscosity. and their mixtures are used in antistrip formulations and asphalt-in-water emulsions.and bis-amidoamines. and functional additives. 24 . 12. to separate alkenes from thermally-cracked petroleum products (20). for example. as part of a composition used as an antioxidant to control fouling (19). 11. Specific ethyleneamine derivatives can also be used for water clarification (16. mobility. demulsifiers.

Cationic formaldehyde. made by the reaction of ethyleneamines with epichlorohydrin (9). incorporate ethyleneamines such as DETA. TETA. and paper coatings (21). The cationic formaldehyde resins. and/or TEPA in the resin backbone to provide substantivity to the cellulose fibers in paper. ethylenebis(stearamide). added to the beater stock to improve the wet strength of tissue. packaging paper products. to make nonacidic papers. antistatic agents (17-20). Improved rates of EDA recovery (25) have also been developed for EDA-sulfide pulping processes (26. adipic acid and epichlorohydrin (37). Numerous modifications of this resin type have been reported (4. and polyamine resins. these types of paper wetstrength resins have been decreasing in popularity due to the adverse health effects associated with formaldehyde. Ethyleneamines are also used in the preparation of certain flocculating agents (13). and acidic conditions required by modified formaldehyde resins. Polyamine wetstrength resins. are also used. 6. These resins can be used under less corrosive neutral or alkaline conditions. 27). both urea. Even though they tend to be less expensive. The bis-amide made by reacting EDA with stearic acid. 8). 11) and polyamines (12). 2). The most popular paper wet strength resins are the modified polyamides typically made with DETA. polyamide. waterproofing and sizing compounds (14-16). is used as a defoamer in paper mill operations. toweling. The sulfur-free delignification of wood chips with EDA-soda liquors has received some interest in the past few years (22-24). represent a major end use for ethyleneamines.Resins and Additives for Pulp and Paper Ethyleneamine-based chemicals are used widely in the paper industry to impart specific functional characteristics to the finished paper. 25 . rather than the Certain pigment retention and drainage additives made with ethyleneamines include various polyamides (10.and melamine-formaldehyde types (1.

grouts. 26 . It is prepared by first reacting EDA with two moles of acetic acid to form the bis-amide. Although the ethyleneamines themselves are often used as the curing agent or part of a curing agent package. (1). and a polyamine. handling. which is then reacted with two moles of acetic anhydride to form the tetra-amide. respectively. patibility with liquid epoxy resins (9-13). Bleach Activators Tetraacetylethylenediamine (TAED) has been widely adopted for use in home laundry products as an activator for peroxygen bleaches. Most of the amidoamines and reactive polyamides contain significant levels of imidazoline structure. adhesives.Epoxy Curing Agents All the commercial ethyleneamines are used either neat or as derivatives for curing epoxy resin-based coatings. are widely used for longer pot life and better flexibility. and safety improveAmidoamines and reactive polyamides prepared by condensation of TETA or higher polyamines with fatty acids (3-5) and dimer acids (6. castings. they are commonly modified in various ways to achieve performance. usually by reaction with acrylonitrile. 7). such as ethylene oxide. cyanoethylation. ketimines. The presence of different polyamino functionalities in the higher ethyleneamines allows partial reaction with various modifiers while retaining sufficient primary and secondary amino functionality for reaction with the epoxy resin portion of the system. and tertiary amino functionality to catalyze that reaction. adhesion. to give derivatives providing longer pot life and better wetting of glass (14). which provides improved com- ments. to DETA (2) as shown above. and a variety of other ethyleneamine modifications (15-18). formaldehyde. laminates. made by the reaction of EDA with acetone. For example. and solvent resistance (8). Other modifications of the ethyleneamines include partial reaction with epoxy resin to form a prepolymer. etc. Mannich bases prepared from a phenol. a common modification is the addition of an alkylene oxide.

Metal Ore Processing Certain processes for enrichment of iron and phosphate ores use amidoamines and imidazolines made from ethyleneamines and fatty acids.Chelates and Chelating Agents Polycarboxylic acids and their salts derived from ethyleneamines are used in a variety of applications where specific metal ions interfere with processing. made from EDA. and as ingredients in systems for etching and for stripping nickel and nickel alloy coatings. 27 . chromium. and fibers (9) have also been developed. It should be pointed out that unmodified ethyleneamines also form stable complexes with certain metal ions. 2). 8). They may be made also by reaction of the ethyleneamine with sodium chloroacetate. The most important commercial family of chelating agents is ethylenediamine tetraacetic acid (EDTA) and its various sodium salts. where their metal complexing properties are required. such as zinc and copper. concentrated. These compounds are produced on an industrial scale primarily through the reaction of the ethyleneamine. such as electroplating and electroless metal coating with specific metals and many alloys. made from DETA. 5). or need to be buffered. These same kinds of derivatives can be used for beneficiation of niobium and tantalum ores (3). and the ethyleneamines themselves aid extraction of copper. Chelating resins. and in lead ore processing and recovery operations (5-8). The intermediate polynitrile may either be hydrolyzed in situ (3). This property makes the ethyleneamines useful in specialized applications. These derivatives selectively adhere to silica particles and permit their removal by flotation procedures (1. or separated and hydrolyzed separately (4. with most di. polymers (7. or transported. AEEA and DETA are also used to make similar polyacetic acid or acetate products. has found application recently in chlorine-free paper pulp bleaching to prevent iron from decreasing efficiency of the hydrogen peroxide (6). They operate by forming stoichiometric complexes. and nickel from their sulfide and oxide ores (4). called chelates. sodium or hydrogen cyanide. 2). separated. Diethylenetriaminepentaacetate (DETPA). and formaldehyde in the presence of sodium hydroxide (1.or polyvalent metals.

2). amidoamines derived by the non-cyclicizing reaction between amine and acid. ethoxylated with an average of 17 moles of ethylene oxide. A variety of 2-alkylimidazolines and their salts prepared mainly from EDA or AEEA are reported to have good foaming properties (3-8). 28 . Anthelmintics (Dewormers) Piperazine is the active ingredient in certain veterinary anthelmintic preparations – primarily for combating intestinal worms in poultry and swine. TEPA. The PIP salts have long been the agents of choice for use against roundworms and pinworms (1). The imidazolines are generally converted into amphoteric surfactants for this application by reaction with one or two moles of sodium chloroacetate (9-11).Surfactants and Emulsifiers To prepare surfactants derived from ethyleneamines. improves the soil antiredeposition and clay soil removal properties of certain liquid laundry detergents (13). AEEA-based imidazolines are also important intermediates for surfactants used in shampoos by TETA. amine salts or soaps obtained by simply mixing the amine with a fatty acid (1. The products of a reaction between DETA. or TEPA and fatty acids also function as water-in-oil or oil-in-water emulsifiers (12). and the imidazoline formed by the reaction under vacuum at virtue of their mildness and good foaming characteristics. elevated temperature to remove two moles of water are all used.

and impart fluffiness. Softeners based on bis-imidazoline compounds are also prepared by condensing TETA or TEPA with fatty acids (7) or triglycerides (8). followed by quaternization with dimethyl sulfate. made from DETA and fatty acids. The amino esters. 2). or reacted with ethylene oxide (3) to convert the central secondary amine group to a tertiary amine. or sodium chloroacetate. Softeners are added to the home washing machine during a rinse cycle or as part of a detergent/softener combination product. “softer” or more pleasing to the touch. These intermediates are then quaternized. as well as their quaternized derivatives. such as AEEA. or to the clothes dryer. Softeners also act as antistatic and antisoiling agents. which gives amphoteric softeners (9). that are either cyclized to the corresponding imidazoline by further dehydration. are more subject to hydrolysis than the amidoamine and imidazoline compounds. they have gained some popularity where environmental biodegradation concerns outweigh their The most common ethyleneamine-based fabric softeners are bis-amidoamines. 29 . As a result.Fabric Softeners Softeners are commonly added to textile materials to make them less harsh. Amino esters are made from acids and an amino alcohol. generally with dimethyl sulfate. Softening agents based on DETA and TEPA are also used in industrial textile processing operations (1. decreased storage stability and performance. to yield compounds that can be formulated into softener products for home laundry use (4-6).

However. was found to be unstable. preventative. prepared from EDA and stearic acid. They are used on many fruit. rust. primary commercial products. It is used as the acetate salt for control of apple scab and cherry leaf spot. The EBDCs are prepared by reacting EDA with carbon disulfide in the presence of an aqueous base. Other materials based on EDA have also been suggested as fungicides.Fungicides The ethylenebisdithiocarbamates (EBDCs) are a class of broad-spectrum. and blight. vegetable. 30 . and grain crops for prevention of mildew. A 2:1 EDA-copper sulfate complex has been suggested for control of aquatic fungi (10). Zineb and maneb are normally formed by the addition of zinc or manganese salts to nabam solutions. The zinc (zineb) and manganese salts (maneb) are especially effective (1-7) and are today the azoline (9). The most important of the imidazoline type (8) is 2-heptadecyl-2-imidS CH2–NH–C–S–Na H2C–CH2–CH2–NH2 + CS2 + 2NaOH CH2–NH–C–S–Na S + 2 H2O This sodium derivative. it is stabilized by conversion to certain other divalent metal salts. nabam. contact fungicides first used in the early 1940’s. The ammonium (amobam) and mixed zinc and manganese (mancozeb) salts are also known. potato. scab.

DETA. ceramics. and surface gloss enhancer. viscosity regulator. and mothproofing (7). ion exchange resins. catalysts (TEDA [triethylenediamine] is a significant example). gas and water treating. They include coal-oil emulsification and coal extraction. shrinkproofing wool (5). and for etching polyimide films. Polymers and Elastomers EDA is a key component of the polymer in spandex fiber. 31 . as precursors for certain compounds providing durable press (3). plaster systems. TETA has been recommended as a curing agent for furfural resin binders in foundry molds and molded graphite. functional fluids. light stabilization of spandex fibers (4). The bisamidoamine condensate made from TETA or TEPA and stearic acid is used as a defoamer in certain textile treatment baths. EDA is used in preparing silane and silanol compounds that improve the adhesion between inorganic surfaces and polymer films. and polyol starters. including the treatment of a wide variety of natural and synthetic fibers for modification of certain properties (1. preservative. and TEPA (8-10). Dye assist compounds for synthetic fibers have been derived from EDA. Other Applications Ethyleneamines find application in numerous other specific industries. to reduce static in polystyrene foam. fire retardants. TETA. Ethyleneamines find application in vulcanization processes for certain rubbers (1-11). Urethane systems and processes employ certain ethyleneamines and their derivatives as curing agents. EDA specifically can be used as a stabilizer for certain urea resins. polymer concrete and concrete additives. and they are used in styrene-butadiene latex processes to coagulate the low levels of finely-dispersed particles in the reaction medium (12-15). petroleum production. industrial corrosion inhibition. static prevention (6). in phenolic resin curing. 2). Acrylate and other monomer vapors can be efficiently removed from vent streams with scrubber solvents containing TETA. to inhibit isoprene polymerization. stone and concrete coatings. pharmaceuticals. and as a parting material. explosives. EDA reacted with stearic acid makes ethylene-bis(stearamide) (EBS) that is used as an external lubricant for ABS resin and PVC. DETA is a component of Nylon 6 (11). and membranes.Textiles Ethyleneamines are used in the textile-related industries for a variety of applications.

Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 7.005 (1) — (2) 0.51 7.21 8.011 1. We will provide a technical contact to discuss specific questions you might have.57 (5) At 80 °C at 15.896 0.60 Metric Units Average Weight per liter.027 (5) At 80 °C at 15.39 (1) — (2) 8. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 0.15 8.Shipping Data Since governmental regulations are subject to change.30 8.980 0.18 8. kg Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.95 8.27 8.015 — (2) — (2) 0. labeling and container requirements may be obtained by contacting Dow at the numbers on the back of this booklet.56°C 0.031 Product Specifications Product specifications and methods are available upon request.995 1.44 8.991 1. Average Weight per gallon.56°C 7. 65% Piperazine. additional information on shipping data.984 1.949 0.900 0. lb Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.953 0.48 7. 32 .987 1.24 8. Please contact Dow at the numbers on the back of this booklet. 65% Piperazine.47 — (2) — (2) 8.977 0.92 8.

00081 0.00081 0.000943 (4) — (2) 0.00077 at 55°C 0.00110 0. ASTM Method D 56 P = Pensky-Martens Closed Cup.00106 0.00623 (3) 0.000767 (3) Coefficient of Expansion. per °C at 20°C 0. ASTM Method D 93 C = Cleveland Open Cup. and nominal 55gallon drums.00076 0. ASTM Method D 92 TO = Tag Open Cup. ASTM Method D 93 C = Cleveland Open Cup.000951 0.00081 0.00092 0.00086 0.00089 0.00076 — (2) — (2) 0. rail car. ASTM Method D 1310 Product Availability Products are available in bulk ocean tanker.00086 0.00110 0.00794 0.00703 0.00077 Flash Point (6).000792 0.00085 0.00680 (3) 0. per °C 0.00642 (3) 0.00095 (5) — (2) 0. per °C 0. °C Closed Cup 43 T 98 P 149 P 171 P 174 P None T 54 P 102 P 127 P Open Cup 39 TO 107 C 154 C 182 C 229 C 96 C 102 C 121 C 154 C (6) T = Tag Closed Cup. ASTM Method D 1310 ∆kg/liter/∆t 10°C to 30°C. °F Closed Cup 110 T 208 P 300 P 340 P 345 P None T 130 P 215 P 260 P Open Cup 103 TO 225 C 310 C 360 C 445 C 205 C 215 C 250 C 310 C (6) T = Tag Closed Cup.00787 (4) — (2) 0.00106 0.00085 0.00083 0.00080 0.000842 0.000815 (3) 0.00640 (3) Coefficient of Expansion. ASTM Method D 92 TO = Tag Open Cup.00081 0.00077 at 55°C 0.00076 0.00661 0.00077 Flash Point (6).00076 — (2) — (2) 0.00095 (5) — (2) 0.000769 (3) 0. per °C at 20°C 0.∆lb/gal/∆t 10°C to 30°C.000747 (3) 0.00092 0. 33 . ASTM Method D 56 P = Pensky-Martens Closed Cup.00089 0.00083 0. tank truck.00080 0.

since TFE is not a true elastomer. This may lead to low levels of byproducts and increase the color of the product. porous insulation may introduce the hazard of spontaneous combustion if the insulation is saturated with ethyleneamines from a leak or external spill. in dedicated service. Consequently. dedicated processing equipment is recommended. spill absorbents and metal wire mesh (such as that used in vapor mist eliminators). Risk of insulation fires can be reduced by insisting on good housekeeping. or be thoroughly wetted with water and then disposed of in closed. consistent with local and federal regulations. copper and copper-bearing alloys are unacceptable for all ethyleneamine service. and oxygen from the atmosphere may be absorbed by the amines. certain grades of these materials may be acceptable in some storage applications. carbon dioxide. However. A 300 series stainless steel is often specified for pumps. except EDA. and training personnel. transfer lines.. self-heating of ethyleneamines may occur by slow oxidation in other absorbent or high-surface-area media. and either smoldering or a flame may be observed. Modest storage temperature (less than 60°C) and nitrogen blankets will allow the use of carbon steel. heavier ethyleneamines without noticeable impact on product quality. and small agitated tanks. watersaturated containers. dumped filter cake. DETA. Carbon steel transfer lines or agitated equipment will suffer enhanced corrosion because of erosion of the passive film by the product velocity.001 in/yr) at typical storage temperatures. To avoid this situation. nitrogen oxides. However. sometimes rapidly and usually exothermically. but the products will pick up iron and discolor badly. Most commonly used industrial thermal insulating materials are acceptable for ethyleneamine service. TFE is an alternative to elastomers since it is resistant to ethyleneamines. valves. Carbon steel is not recommended for EDA. Recommended gaskets for ethyleneamine service are made of GRAFOIL™ flexible graphite or polytetrafluoroethylene (TFE). minimizing insulated flanges and fittings. like many other combustible liquids. heating coils. or AEEA storage tanks. this may lead to spontaneous combustion. then 300 series stainless steels are recommended for the storage tanks. In some cases. No single elastomer is acceptable for the entire product line.g. Carbon steel with baked phenolic lining is acceptable for storage of many pure ethyleneamines. even at ambient temperature. Also. Galvanized steel. Ethyleneamines can permeate polyethylene and polypropylene.Storage and Handling Ethyleneamines react with many other chemicals. inert atmosphere (such as low CO2-containing nitrogen) will minimize this sort of degradation. e. However. If this cannot be tolerated. 34 . Proper selection of materials of construction for ethyleneamine service is essential to ensure the integrity of the handling system and to maintain product quality. Corrosion is not extreme (<0. it may not always prove suitable as a replacement material. any of these media contaminated with ethyleneamines should be washed with water to remove the amines. maintenance of weather barriers. Closed cellular glass insulation is normally resistant to insulation fires because it is difficult for the ethyleneamines to saturate these materials and also difficult for air to contact the product. Water. Nonmetallic equipment is not normally used for ethyleneamine service. for nonaqueous. Storage under a dry.

Also. may be found in the Material Safety Data Sheets. EDA has the lowest flash point (Tag Closed Cup): 43°C (110°F). At elevated temperatures some product breakdown may be observed in the form of ammonia and the formation of lower and higher molecular weight species. solid amine hydrates may form. Additionally. ethyleneamines exhibit good temperature stability. which can be a nuisance in handling. As commercially pure materials. This degradation increases in rate as the temperature and/or time increases. For additional information. contact Dow at the numbers on the back of this booklet and request our Ethyleneamines Storage and Handling Brochure and/or a technical contact who will discuss specific questions about acceptable materials of construction and storage practices. which causes the carbamates to decompose. Tank vents and safety devices are also susceptible to fouling by solid amine carbamates formed by the reaction of the amines with carbon dioxide. 35 . in certain concentrations. All amine vents should be routed to a safe location and “smoking vents” routed to water scrubbers to capture the vapors. vent lines and safety devices. Vent fouling can be reduced by using nitrogen blankets on storage tanks to exclude atmospheric CO2. Warm water cleanup can reduce the extent of the problem. even in areas where routine processing is nonaqueous. although the amines are water-soluble. heavier ethyleneamines may be stored at elevated temperatures (40-60°C) to ease inplant handling by lowering the viscosity. vent units and relief devices may be steam-traced to maintain 160°C. Ethyleneamines are typically maintained above their freezing points which may require storage above ambient temperatures (particularly EDA and PIP). Storage at elevated temperatures can cause vapors “breathing” from the tank to contain significant concentrations of product. Testing for thermal stability is suggested whenever ethyleneamines are mixed with other materials. as well as recommended safety procedures.The amines do not present any unusual flammability problem at ordinary temperatures. mineral acids contamination). In addition. which are updated as new information becomes available. contact Dow at the numbers on the back of this booklet. This information is of a general nature. For the latest Material Safety Data Sheets on ethyleneamines. Hydrate problems are usually avoided by insulating and heat tracing equipment to maintain a temperature of at least 50°C. Additionally. contaminants can lower the onset of rapid exothermic thermal decomposition (for example. Vent units require periodic inspection to verify that fouling is not occurring and to ensure that seals are functioning properly to exclude air from the tank. Water cleanup of ethyleneamine equipment can result in hydrate problems. Hydrates can plug processing equipment. Health Effects Information on health effects and their management.

which rapidly biodegraded.86 1. Aquatic toxicity measurements showed only moderate toxicity for most of the tested amines. and Standard Methods techniques.84 1.68 1.50 1. These studies were conducted by procedures which follow the EPA. Calculated value based on oxygen required to oxidize the chemical to carbon dioxide and water.75 — — 1. Natural acclimation in a wastewater treatment plant or in the general environment would be expected to increase the rate and extent of biodegradation for the related compounds. EDA. 10.63 Calc.88 1. Nonacclimated domestic sewage microorganisms used as seed. Bacterial inhibition tests indicate that none of these amines tested should be inhibitory to conventional wastewater treatment processes at expected discharge levels of less than 500 mg/L. 65% Aminoethylpiperazine Aminoethylethanolamine Carbonaceous Meas.Ecological Fate and Effects Dow has conducted a series of laboratory studies on the biodegradation and ecological effects of these amines.93 1.86 1.69 — 1. 1.28 1.54 Nitrogenous Calc. and 20..33 1.49 1. Several amines. 36 . ASTM. while the nitrogen converts to and remains as ammonia.13 1. (3) The measured biooxidation as a percent of the total carbonaceous and nitrogenous oxygen demand (sum of calculated carbonaceous and nitrogenous ThOD values) is presented for Days 5.48 1.86 1. with the exception of EDA/DETA studies which used acclimated seed. Ecological Fate and Effects of Ethyleneamines Theoretical Oxygen Demand. Public Health Assoc. (ThOD) mg/mg(1) Product Evaluated Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. The impact of acclimation on the rate and extent of biodegradation is shown by the EDA and DETA acclimated seed data.55 1. (2) Measured in dilution bottle biochemical oxygen demand test published in Standard Methods. The data presented in the following table show that the amines biodegrade slowly. 17th ed.23 (1) Measured by Chemical Oxygen Demand (COD) procedure published in Standard Methods for the Examination of Water and Wastewater.94 1.64 1. 2. The nitrogenous oxygen demand is calculated based on nitrogen being oxidized to nitrate by nitrifying bacteria. showed more toxicity to Daphnia magna with LC50 values ranging from 5 to 40 mg/L. and AEP. DETA. The biooxidation values are calculated as percentage ratio of BOD and ThOD (BOD/ThOD x 100). TETA. (COD) 1. except for EDA and AEEA. Biodegradation was measured by the riversimulating 20-day biochemical oxygen demand (BOD) test using nonacclimated microorganisms. (1989).

% biooxidation Total Carbonaceous(2) Days 5/10/20 68/100/100 A36(6)/A45(6)/A70(6) <5/<5/<5 A23(6)/A46(6)/A70(6) 3/4/9 4/7/12 <5/<5/<5 <10/<10/<10 2/4/7 2/64/90 —/—/— —/—/— —/—/— —/—/— —/—/— —/—/— 1/37/53 >5000 680 — — 4600 1400 >5000 25/37/78 1000 Nitrogenous(3) Days 5/10/20 Bacterial (4) Inhibition IC50. and request that t hey do the same. you should obtain available product safety information and take necessary steps to ensure safety of use. applicable laws and regulations. The customer should furnish the information in these publications to its employees. medical device. understand. contact Dow at the numbers on the back of this booklet. For Material Safety Data Sheets and other product safety information. No chemical should be used as or in a food. or cosmetic until the user has determined the suitability and legality of the use. or any other users of the product(s). medical device. mg/L 48-hour 96-hour Daphnia magna Fathead Minnow 5 (4-6) 17 (15-19) 40 (35-50) — — 90 (80-110) 36 (25-50) 110 (90-130) 210 (190-230) 260 (220-310) 330 (280-400) 310 — 720 (640-800) 560 (500-620) 515 (470-560) (4) Determined by turbidity/growth procedures where the median inhibition concentration (IC50) is measured after 16 hours of incubation with sewage microorganisms. No nitrification was measured in the acclimated systems. 37 . Dow requests that the customer read. drug. (6) Biooxidation values for EDA and DETA are taken from tests with acclimated microorganisms. (5) Fathead minnows and Daphnia magna bioassays were conducted using procedures published by EPA and ASTM. Before handling any other products mentioned in the text. and customers. contractors. Biochemical Oxygen Demand(2). and comply with the information contained in this publication and the current Material Safety Data Sheet(s). The 95% confidence limits (95% CL) are shown in parentheses. or in a product or process in which it may contact a food. or cosmetic.Product Safety When considering the use of any Dow products in a particular application. drug. Since government regulations and use conditions are subject to change. it is the user’s responsibility to determine that this information is appropriate and suitable under current. mg/L Aquatic Toxicity (5) LC50. you should review our latest Material Safety Data Sheets and ensure that the use you intend can be accomplished safely.

105 175. it is the responsibility of the user of an ethyleneamine as a Direct or Indirect Food Additive to read and understand any applicable FDA regulations in Title 21 of the Code of FDA Regulation Ethylenediamine 21 CFR Permitted Uses 173. Crosslinker with epichlorohydrin to make ion-exchange resins used in the processing of food.300 175. and dry food.4’-iso-propylidenediphenol epichlorohydrin epoxy resins. transporting. Modifier for melamine-formaldehyde resins for use as the basic polymer in cellophane. and as a resin to anchor coatings to substrate. and dry food.1200 177. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane.2600 178. aqueous. 175. aqueous. Urea-formaldehyde resins chemically modified with polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food.0 ppm based on the weight of raw cane or beets processed. However.1200 177.320 175.300 177.300 175.0 ppm based on the weight of raw cane processed.170 176. sulfanilic acid. Component of adhesives used in articles intended for packaging.320 173. as a modifier for melamine-formaldehyde resins used in cellophane. Modifier for urea-formaldehyde and melamine-formaldehyde resins for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with fatty. Formulation of defoaming agents used in the manufacture of paper and paperboard prior to and during the sheet forming operation. Accelerator in vulcanization of rubber articles intended for repeated use.25 173. not to exceed 1. applied to the sugar mill grinding. or holding food. aqueous.300 175.1010 177. and/or diffusor systems at a maximum level of 1.180 176.170 176.380 175. crusher.170 176. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for modifying urea-formaldehyde resins used as the basic polymer and as a resin to anchor coatings to the substrate in the manufacture of food-packaging cellophane. applied to the sugar mill grinding.1200 177.1210 177. and other listed amines.390 176. Adjuvant in the preparation of slimicides used as antimicrobial agents to control slime in the manufacture of paper and paperboard. Catalyst activator in semirigid and rigid acrylic and modified acrylic plastics. crusher. Catalyst and crosslinking agent for epoxy resins used in resinous and polymeric coatings applied as a continuous film or enamel over a metal substrate or applied as a continuous film or enamel to any suitable substrate provided that the coating serves as a functional barrier between the food and the substrate and is intended for repeated food-contact use. Polyamide-epichlorohydrin resins prepared by reacting adipic acid or other acids with diethylenetriamine to form a basic polyamide and further reaction of the polyamide with other materials to form water-soluble thermosetting resins for use in the manufacture of paper and paperboard.3120 38 .180 176. Modifier for urea-formaldehyde and melamine-formaldehyde resins used as the basic polymer in resinous and polymeric coatings on a metal substrate. Component in an antimicrobial formulation used in cane sugar mills.180 176. Catalyst for epoxy resins used as the food contact surface of paper and paperboard in contact with fatty.170 176. and/or diffusor systems at a maximum level of 2.180 176. at a level not to exceed 0.1200 177. Catalyst for epoxy resins and component of polyamides for use in xylene-formaldehyde resins condensed with 4.180 176.FDA Status Dow provides the following FDA Status Summary for the convenience of our customers.5 wt% based on the monomers. Component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food (as a crosslinking agent in polymerization). Polyamides from vegetable oil acids and sebacic acid for use in side seam and can-end cements.180 176. and dry food. Catalyst for epoxy resins and component of polyamides for use in zinc-silicon dioxide matrix coatings. Modifier for amino resins used as a component of the coated and uncoated food-contact surface of paper and paperboard in contact with fatty.300 Preparation of ion-exchange membranes used in the processing of grapefruit juice. Polyamides from dimerized vegetable oils for use as adjuncts for epoxy resins. Additive in the production of animal glue.20 173.210 176.5 wt% of the rubber product.105 175. Component in an antimicrobial formulation used in cane sugar and beet sugar mills. Modifier for urea-formaldehyde resins for use as the basic polymer in cellophane and as a resin to anchor coatings to substrate. Polyamides formed by reaction with dimerized vegetable oil acids for use as components of food-packaging adhesives. Catalyst for epoxy resins and component of polyamides for use in making closures with sealing gaskets.

it is the responsibility of the user to determine that any such use is suitable. Furthermore. safe.Federal Regulations (21 CFR) to determine any limitations or restrictions on the proposed use. Diethylenetriamine (EDA) Triethylenetetramine (DETA) ✔ ✔ Tetraethylenepentamine (TETA) ✔ Aminoethylethanolamine (TEPA) ✔ (AEEA) ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ 39 . and FDA-compliant.

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